alpha,alpha'-Dichloro-p-xylene → Trichloro{[4-(chloromethyl)phenyl]methyl}silane

HRID 1937096Notes

Reaction equation

HRID 1937096 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][CH:4]=1.[Cl:11][SiH:12]([Cl:14])[Cl:13]>[Cl-].C([P+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Si:12]([Cl:14])([Cl:13])[Cl:11])=[CH:5][CH:4]=1.[Cl:11][Si:12]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Si:12]([Cl:14])([Cl:13])[Cl:11])=[CH:5][CH:4]=1)([Cl:14])[Cl:13]

Participants

6

Reactant 2

HCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 24811Trichlorosilane

Product 2

HCID 12584568[1,4-Phenylenebis(methylene)]bis(trichlorosilane)Yield 25%HCID 12584569Trichloro{[4-(chloromethyl)phenyl]methyl}silaneYield 30%

Reagents, catalysts & solvents 2

HCID 75311Tetrabutylphosphonium chlorideCatalystHCID 241BenzeneSolvent

Procedure

In the same apparatus and procedure as Example 1 above, 0.059 g (0.20 mmol) of tetrabutylphosphonium chloride, 0.35 g (2.0 mmol) of 1,4-bis(chloromethyl)benzene, 1.35 g (10.0 mmol) of trichlorosilane, and 10 ml of dried benzene were reacted at 150° C. for 2 hrs. The resulting mixture was distilled to give 0.16 g of 1-chloromethyl-4-(trichlorosilylmethyl)benzene (yield; 30%) and 0.19 g of 1,4-bis(trichlorosilylmethyl)benzene (yield; 25%).

Workup

  1. distillationThe resulting mixture was distilled

Sources & evidence

ORD record
ord-91a2cebeed544687a9422356c4a82026
Source dataset
uspto-grants-2002_05
Patent number
US06392077B1

Reaction notes

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